Hydrochloric Acid → (+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

HRID 853

반응식

HRID 853 반응식
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C([N:14]1[CH:18]([CH2:19][OH:20])[CH2:17][O:16][C:15]1=[O:21])C.Cl.N1C=CC=[CH:25][CH:24]=1>[Cl-].[Na+].O>[CH2:24]([C:18]1([CH2:19][O:20][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH2:17][O:16][C:15](=[O:21])[NH:14]1)[CH3:25]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 19694098(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

생성물 1

HCID 18968885(+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a solution of brine and 1N HCl, stirred until solids appeared, filtered and washed with diethyl ether to give 194.6 g of a beige solid as the title product. 1H NMR consistent with the proposed structure.

후처리

  1. customto come to room temperature
  2. stirringstirred until solids
  3. filtrationfiltered
  4. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-85a305aeebfc4263a0d5dfa4da2ff2f2
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723458

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